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WO2024138275A1 - Formulations fongicides pour combattre des maladies d'intérêt agronomique et leurs procédés de production - Google Patents

Formulations fongicides pour combattre des maladies d'intérêt agronomique et leurs procédés de production Download PDF

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Publication number
WO2024138275A1
WO2024138275A1 PCT/CL2022/050142 CL2022050142W WO2024138275A1 WO 2024138275 A1 WO2024138275 A1 WO 2024138275A1 CL 2022050142 W CL2022050142 W CL 2022050142W WO 2024138275 A1 WO2024138275 A1 WO 2024138275A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation according
biopolymer
agent
coupling agent
pmpi
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CL2022/050142
Other languages
English (en)
Spanish (es)
Inventor
Luciano Francesco DIBONA VILLANUEVA
Denis Alberto FUENTEALBA PATIÑO
Héctor Antonio VALDÉS GÓMEZ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pontificia Universidad Catolica de Chile
Original Assignee
Pontificia Universidad Catolica de Chile
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pontificia Universidad Catolica de Chile filed Critical Pontificia Universidad Catolica de Chile
Priority to PCT/CL2022/050142 priority Critical patent/WO2024138275A1/fr
Publication of WO2024138275A1 publication Critical patent/WO2024138275A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • LAAM light-activated antimicrobial materials
  • the search focused on documents related to antimicrobial formulations that inhibit the growth of pathogens of agronomic interest. More specifically, the search focused on formulations comprising chitosan and a photoactivatable antimicrobial compound, to be used as an antimicrobial agent against pathogens of the genus Penicillium, Botrytis and Rhizopus. In general, the analysis carried out suggests that there is no formulation that can be used as an antimicrobial that has the same characteristics, composition and/or the same excipients, compared to the formulation described in the present invention.
  • the preparation of the CH-RF compound is carried out in 3 general steps: a) conjugate a photoactivatable agent with a coupling agent obtaining a derivative A, b) treat a biopolymer with acid and a coupling agent, obtaining a compound B, c) react the derivative A obtained in step (a) and the compound B obtained in step (b) in a solvent, for 72 hours; precipitate with ethanol, filter and dry.
  • the bacterial pathogens of the formulation are selected from the genera Penicillum and Botrytis.
  • Protoporphyrin IX is mixed with EDC and CH, ignoring step (a).
  • this describes the fungicide formulation to combat fungal infections corresponding to gray rot, green rot and soft rot, where the pathogens to be combated are selected from Botrytis cinerea and Penicilium digitatum.
  • the synthesis results and photophysical properties presented below are focused on the fungicidal formulations of the present invention, and where the results and technical advantages are compared with the previous state of the art, for example, patent application CL 201903654 developed by the same inventors.
  • CH-PPIX compound which presents fungicidal activity when used at a dose of 0.007% w/v, being much lower (100-200 times) than similar formulations based in chitosan.
  • the fungicidal effect evaluation results are completely new results for the fungicidal formulations of the present invention.
  • the RF-PMPI precursor was synthesized with a yield of 52% and the synthesis volume was scaled 933 times. In addition, the purification steps were reduced from 6 to 4, obtaining a pure product that is key to the synthesis of the conjugate called CHRF100.
  • CHRF100 was synthesized with a reaction yield of 46% and recovery yield of 97.7%, increasing the synthesis scale 25.8 times. It was possible to replace the purification steps of dialysis and lyophilization with precipitation, a much simpler and less expensive process than the one used previously.
  • LEAPs Light Enhanced Antimicrobial Polymers
  • the absorption and emission spectra of the LEAPs in aqueous solutions, the photostability and the photoactivity of the LEAPs were determined.
  • CHRF100 an absorption maximum of 450 nm and a fluorescence emission maximum of 535 nm were determined.
  • CHPPIX20 an absorption maximum of 405 nm and an emission maximum of 633 nm were determined.
  • CHRF100 has greater photostability than the photoactive agent alone under the experimental conditions used, not presenting greater light-induced degradation in the measured period of time.
  • CHPPIX20 it has greater photostability than the photoactive agent alone under the experimental conditions used, presenting almost no light-induced degradation in the measured period of time.
  • CHRF100 has a slightly lower capacity to generate reactive oxygen species compared to the photosensitizer alone.
  • CHPPIX20 has a higher photoactivity than the photosensitizer alone.
  • the severity of the damage is measured according to the scale described by Ozkan (2011; Figure 1 1), where it is evaluated with a scale from 0 to 5, where 0: It is a healthy berry, 1: Berry with rot (watery appearance and browning) but absence of visible mycelium, 2: Berry with rot and presence of mycelium, 3: Berry with moderate amount of mycelium and/or more than one point of infection, 4: Berry with infection equal to or less than 50% of the surface and 5: Berry with more than 50% infection.
  • the severity of the infection obtained from the previous scale is converted into a percentage by multiplying the number of infected berries that are between levels 1 and 5, by the severity detected on the scale (1,2, 3, 4, 5) , are added and then divided by the total number of berries in each treatment.
  • Trials were carried out where the inoculated samples were evaluated, with treatments of CHPPIX20 at concentrations of 0.7%; 0.07%; 0.007% w/v; CHRF100 at a concentration of 0.7% w/v and the control treatment with distilled water.
  • the LEAPs were mixed with the Bond adjuvant at a concentration of 0.1% v/v. After the application of the LEAPs, the berries are immediately placed under the corresponding light for 30 minutes, turning them after 15 minutes.
  • Figure 7b shows that in in vitro experiments for the growth inhibition of Botrytis cinerea, the new conjugate (CHRF100) needs a concentration of 0.003% w/v to have a total inhibition effect. That is, lower than the concentration used under similar conditions, with the old conjugate.
  • Figure 8 shows the same effect indicated above.
  • Figure 8 a shows that in in vitro experiments for the inhibition of growth of Penicillium digitatum, the old conjugate needs a concentration of 0.005% w/v to have an evident effect.
  • Figure 8b shows that, in in vitro experiments for the inhibition of growth of Botrytis cinerea, the new conjugate (CHPPIX20) needs a concentration of 0.03% w/v to have a total inhibition effect, that is, , lower than the concentration used under similar conditions, with the old conjugate.
  • Figure 9 shows in vivo results of the conjugates of the new invention.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des formulations fongicides pour combattre des infections fongiques dans des cultures d'intérêt agronomique, comprenant une quantité efficace d'un conjugué entre un biopolymère et un agent photo-activable. L'invention concerne également le procédé d'élaboration desdites formulations ainsi que leur utilisation pour combattre des infections fongiques.
PCT/CL2022/050142 2022-12-29 2022-12-29 Formulations fongicides pour combattre des maladies d'intérêt agronomique et leurs procédés de production Ceased WO2024138275A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CL2022/050142 WO2024138275A1 (fr) 2022-12-29 2022-12-29 Formulations fongicides pour combattre des maladies d'intérêt agronomique et leurs procédés de production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CL2022/050142 WO2024138275A1 (fr) 2022-12-29 2022-12-29 Formulations fongicides pour combattre des maladies d'intérêt agronomique et leurs procédés de production

Publications (1)

Publication Number Publication Date
WO2024138275A1 true WO2024138275A1 (fr) 2024-07-04

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CL2022/050142 Ceased WO2024138275A1 (fr) 2022-12-29 2022-12-29 Formulations fongicides pour combattre des maladies d'intérêt agronomique et leurs procédés de production

Country Status (1)

Country Link
WO (1) WO2024138275A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008130181A1 (fr) * 2007-04-23 2008-10-30 Korea Institute Of Science And Technology Nouveau photosensibilisateur fondé sur des conjugués dérivés de polymère-photosensibilisateur pour thérapie photodynamique
CL2019003654A1 (es) * 2019-12-12 2021-08-13 Univ Pontificia Catolica Chile Conjugados entre un biopolímero y un agente antimicrobiano fotoactivable para combatir enfermedades fúngicas de interés agronómico y métodos de producción de dichos conjugados

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008130181A1 (fr) * 2007-04-23 2008-10-30 Korea Institute Of Science And Technology Nouveau photosensibilisateur fondé sur des conjugués dérivés de polymère-photosensibilisateur pour thérapie photodynamique
CL2019003654A1 (es) * 2019-12-12 2021-08-13 Univ Pontificia Catolica Chile Conjugados entre un biopolímero y un agente antimicrobiano fotoactivable para combatir enfermedades fúngicas de interés agronómico y métodos de producción de dichos conjugados

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEN, C. ET AL.: "Chitosan Nanoparticles for Antimicrobial Photodynamic inactivation: Characterization and In Vitro Investigation", PHOTOCHEMISTRY AND PHOTOBIOLOGY, vol. 88, 2012, pages 570 - 576, XP055834719, DOI: 1 0.1111/j.1751-1 097.2012.011 01.x *
DIBONA-VILLANUEVA LUCIANO, FUENTEALBA DENIS: "Novel Chitosan–Riboflavin Conjugate with Visible Light-Enhanced Antifungal Properties against Penicillium digitatum", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 69, no. 3, 27 January 2021 (2021-01-27), US , pages 945 - 954, XP093192931, ISSN: 0021-8561, DOI: 10.1021/acs.jafc.0c08154 *
DIBONA-VILLANUEVA LUCIANO, FUENTEALBA DENIS: "Protoporphyrin IX–Chitosan Oligosaccharide Conjugate with Potent Antifungal Photodynamic Activity", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 70, no. 30, 3 August 2022 (2022-08-03), US , pages 9276 - 9282, XP093192940, ISSN: 0021-8561, DOI: 10.1021/acs.jafc.2c01644 *
PEI JILIU, ZHU SHENGYU, LIU YU, SONG YUKANG, XUE FENG, XIONG XIAOHUI, LI CHEN: "Photodynamic Effect of Riboflavin on Chitosan Coatings and the Application in Pork Preservation", MOLECULES, MDPI AG, CH, vol. 27, no. 4, 17 February 2022 (2022-02-17), CH , pages 1355-1 - 1355-14, XP093192951, ISSN: 1420-3049, DOI: 10.3390/molecules27041355 *
Q. MESQUITA MARIANA, J. DIAS CRISTINA, P. M. S. NEVES MARIA, ALMEIDA ADELAIDE, F. FAUSTINO M.: "Revisiting Current Photoactive Materials for Antimicrobial Photodynamic Therapy", MOLECULES, vol. 23, no. 10, 2018-09-21, pages 2424-1 - 2424-47, XP055834728, DOI: 10.3390/molecules23102424 *

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